How can I fly for free?

1- Points

You can accumulate points (especially easy if you’re American… harder if you’re not) and redeem them in the most advantageous way possible.

However, contrary to popular belief, I think that this is NOT the best way for most people to save money on travel.

No matter how good you are, you’ll still spend some money either on the cards, on booking fees, on fuel surcharges, etc, but if you handle it right you can still save money this way.

However, most people will justify extra spending in the name of getting points, or misunderstand the redemption conditions, or end up not using their points or will use them at a loss.

Some people win at this game, but most end up with a false sensation of value that doesn’t quite pay off- which is exactly the point of loyalty programs in the first place (get it? The POINT?)

2- Work for an airline!

Yup, everyone forgets to talk about this, but airline employees get either free or heavily subsidized flights. You might even get to sit in first class.

You don’t need to work as a flight attendant or baggage handler to do it- airlines have thousands of staff at the head office: HR, accounting, pricing, legal, etc.

Cheap or free flights are a great perk, but of course it comes at a price: you need to show up for work. No, airlines don’t give unlimited vacation… if they did there would never be anyone in the office!

There is also the trade-off of flying standby (remember that time we almost got stranded in Bogota??) But being able to plan last-minute trips with an extra jolt of wondering whether you’ll get a seat is pretty exciting; so we’ll call that a moot point.

So, if you need to work somewhere and want to take weekend trips to Tokyo, working for an airline is great. If you want to travel around the world for a year, this is probably not the right “hack” for you.

3- Just pay for your damn flights.

Be flexible, use a tool like Skyscanner or Kayak to find the cheapest rates, and only fly when you need to.

Consider all transit options (bus, train, plane, boat, car, rideshare, etc) and only travel when it’s worth it for you.

…and the winner is?

I’ve done all 3 of these options, and while standby is great and sometimes points can save you some money, I believe that door #3 is by far the best (and possibly cheapest) option for me right now.

No commitments, no purchases, no constraints except the price and whether I’m willing to pay it. That freedom is worth it!